Toluene-4-sulfonic acid (2S,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-butyl ester

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Chemical Name:Toluene-4-sulfonic acid (2S,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-butyl ester
CAS No.:114972-46-2
Molecular Formula:C₁₈H₃₂O₅SSi
Molecular Weight:388.601
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2S,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-butyl ester

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Chemical Property of Toluene-4-sulfonic acid (2S,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-butyl ester

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Technology Process of Toluene-4-sulfonic acid (2S,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-butyl ester

There total 2 articles about Toluene-4-sulfonic acid (2S,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

: 114972-45-1
(2S,3S)-4-[(tert-butyldimethylsilyl)oxy]-3-methylbutane-1,2-diol

: 98-59-9
p-toluenesulfonyl chloride

: 114972-46-2
Toluene-4-sulfonic acid (2S,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-butyl ester

Guidance literature:: With pyridine; at -20 ℃;
DOI:10.1016/S0040-4020(01)90315-1

Reference yield:

: 114972-44-0
(2S,3S)-1-(benzyloxy)-4-[(tert-butyldimethylsilyl)oxy]-3-methylbutan-2-ol

: 114972-46-2
Toluene-4-sulfonic acid (2S,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / H₂ / Pd(OH)2/C / ethanol / 4 h

2: 92 percent / pyridine / -20 °C

With pyridine; hydrogen; palladium dihydroxide; In ethanol;
DOI:10.1016/S0040-4020(01)90315-1

Reference yield:

: 114972-46-2
Toluene-4-sulfonic acid (2S,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-butyl ester

: 114972-67-7,115016-25-6
(2E,5E,8E)-(4R,7S,12S,13R)-13-Benzyloxymethoxy-7-methoxy-4,8,12-trimethyl-4-(tetrahydro-pyran-2-yloxy)-tetradeca-2,5,8-trienoic acid

Guidance literature:: Multi-step reaction with 11 steps

1: 84 percent / LiB(Et)3H / tetrahydrofuran / 0.5 h / 0 °C

2: 72 percent / diisopropylethyl amine / CH₂Cl₂ / Ambient temperature

3: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1) 0 deg C, 1 h, 2) room temperature, 2 h

4: 92 percent / CBr₄/PPh₃ / CH₂Cl₂ / 1 h / -40 °C

5: 80 percent / tetrabutylammonium bromide / dimethylformamide / 8 h / 40 °C

6: 1) butyllithium, HMPA, / 1) THF, hexane, -40 deg C, 90 min, -65 deg C, 10 min, 2) THF, -65 deg C - -10 deg C, 2.5 h

7: 87 percent / Na₂HPO₄, 6percent Na-amalgam / methanol / 2 h / Ambient temperature

8: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1) 0 deg C, 1 h, 2) room temperature, 2 h

9: 90 percent / oxalyl chloride, DMSO, triethylamine / CH₂Cl₂ / -60 °C

11: 98 percent / 1 M aq. LiOH / tetrahydrofuran; H₂O / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; oxalyl dichloride; carbon tetrabromide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)90315-1